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The Unlikeliest Victory: Lifelong Friends Bet on Last Place and Win Big

  • Nishadil
  • January 12, 2026
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  • 4 minutes read
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The Unlikeliest Victory: Lifelong Friends Bet on Last Place and Win Big

From Last Place to $100K: A Friendship's Unconventional Circa Million Triumph

Two lifelong friends from Massachusetts, Brad and Paul, defied conventional wisdom in the Circa Million V, intentionally aiming for last place and walking away with a surprising $100,000 prize. Their unique strategy, born from years of shared sports betting, proved an unexpected triumph.

Brad and Paul, two inseparable friends since their kindergarten days in Massachusetts, have always shared a passion for sports. And, perhaps just as passionately, they've shared an interest in sports betting. But their latest triumph isn't your run-of-the-mill story of picking winners; oh no, this tale takes a delightful, rather unconventional twist. These gentlemen, now in their early fifties, just scooped a cool $100,000 in the prestigious Circa Million V contest, not by coming in first place, but by doing something truly unexpected: they intentionally finished dead last.

You see, for years, they'd tried their hand at various sports betting contests, including the well-known SuperContest, with results that, let's just say, weren't exactly life-changing. There's a certain wisdom that comes with experience, and after a while, they began to ponder a different approach. The top prize in these massive contests often feels like a lottery win, a distant dream for most. But the "booby prize," the payout for finishing at the very bottom? That, they reasoned, might just be a more achievable target. And so, their peculiar, yet ultimately brilliant, strategy for the Circa Million V was born.

For those unfamiliar, the Circa Million V is a high-stakes pro football handicapping contest where participants pick five NFL games against the spread each week. While the ultimate glory (and a multi-million dollar payday) goes to the overall winner, Circa also smartly offers a substantial incentive for the final position. A six-figure sum for finishing last isn't just a consolation prize; it's a legitimate, life-enhancing amount of money. And for Brad and Paul, who were diving into the Circa Million for the very first time, this unconventional path offered a compelling, albeit counterintuitive, allure.

Their process became a weekly ritual, often taking place at Brad's house, a hub for their shared love of sports. Their mission? To identify the five most reliably bad picks each week. This wasn't about finding longshot underdogs who might cover; it was about pinpointing teams and matchups that seemed destined to fail, or at least, fail to cover the spread. It sounds easy, doesn't it? Just pick losers. But, as they quickly discovered, consistently picking five losers in the NFL, week after week, is surprisingly challenging. The NFL, after all, is a league of unpredictability, where even the most seemingly certain outcomes can flip on a dime.

Indeed, their journey wasn't without its nail-biting moments and frustrating setbacks. There were weeks when their meticulously chosen "bad" picks would, against all odds, actually win or cover, completely throwing a wrench into their last-place aspirations. Imagine the agony: you're actively rooting for your picks to lose, only to see them pull off an unexpected victory! They even had to adjust their strategy mid-season, fine-tuning their process to ensure they maintained their precarious position at the bottom of the leaderboard. It truly became a delicate dance, balancing the art of the "bad" pick with the inherent chaos of football.

As the season wound down, the tension mounted. Every pick mattered, not for winning, but for ensuring they stayed exactly where they wanted to be: last. When the final scores were tallied and their last-place finish was confirmed, a wave of elation washed over them. It was a victory unlike any other, a testament to their shared vision, their dedication, and perhaps a healthy dose of shared stubbornness. The $100,000 prize wasn't just money; it was the sweet validation of a strategy most would deem crazy.

So, what's next for these innovative friends? Well, they're already eyeing next year's contest, no doubt ready to refine their unique approach. Their story isn't just about a big win; it's about the enduring power of friendship, the joy of a shared pursuit, and the refreshing realization that sometimes, the most unexpected path can lead to the greatest rewards. Who knew that finishing last could feel so incredibly good?

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